ChemicalBook CAS DataBase List N-Boc-1-aminocyclobutanecarboxylic acid

N-Boc-1-aminocyclobutanecarboxylic acid synthesis

5synthesis methods

Product Name:N-Boc-1-aminocyclobutanecarboxylic acid
CAS Number:120728-10-1
Molecular formula:C10H17NO4
Molecular Weight:215.25

Under stirring, add 1-aminocyclobutylcarboxylic acid (500mg, 4.34mmol) to 10mL of 0.5M sodium hydroxide solution, and add 10mL of 1,4-dioxane and di-tert-butyl dicarbonate (1.42g, 6.51 mmol), react for 15 hours. Extract with diethyl ether (20 mL × 2), add hydrochloric acid dropwise until the pH of the aqueous phase is 4, and extract with ethyl acetate (30 mL × 3). The organic phases were then combined, washed with saturated sodium chloride solution (20mL×2), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain the product N-Boc-1-aminocyclobutanecarboxylic acid (750mg, white solid), yield:80.6%.

24424-99-5 Synthesis

24424-99-5
840 suppliers
$13.50/25G

22264-50-2 Synthesis

22264-50-2
284 suppliers
$11.00/1g

120728-10-1
315 suppliers
$6.00/1g

Yield:120728-10-1 75%

Reaction Conditions:

with sodium hydrogencarbonate in 1,4-dioxane;water at 0 - 20; for 12 h;

Steps:

4.1 Step 1: Synthesis of 1-((tert-butoxycarbonyl)amino)cyclobutane-1-carboxylic acid
To a stirred solution of 1-aminocyclobutane-1-carboxylic acid (2 g, 17 mmol) in 1,4- dioxane: H₂O (20: 20 mL), were added NaHCO₃ (4.4 g, 57 mmol) and (Boc)₂O (4.5 g, 20.4 mmol) at 0°C and stirred the reaction mixture for about 12 hours at room temperature. After complete conversion of starting material, the reaction mixture was washed with EtOAc (30 mL) to remove the impurities, then aqueous layer was acidified with 1N HCl (PH =2-3) and extracted with CH₂Cl₂ (2x40 mL). The combined organic extracts were washed with water, brine, dried over Na₂S0₄, filtered and evaporated under reduced pressure. The crude residue was purified by silica gel column chromatography by using 35 % EtOAc: n-Hexane as an eluent to afford the desired product (2.8 g, yield: 75%) as an off white solid. 1H MR (300 MHz, CD₃OD): δ 2.62-2.53 (m, 2H), 2.25-2.15 (m, 2H), 2.05-1.97 (m, 2H), 1.42 (s, 9H); ES Mass: 238.04 [M+Na]⁺.

References:

HETERO RESEARCH FOUNDATION;BANDI, Parthasaradhi Reddy;KURA, Rathnakar Reddy;GAZULA LEVI, David Krupadanam;ADULLA, Panduranga Reddy;NEELA, Sudhakar;MOGILI, Narsingam WO2017/21922, 2017, A1 Location in patent:Page/Page column 26

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